Podcast

21 Hats Podcast

A weekly conversation on what it takes to run a business.

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Latest episodes

  1. Best of: Selling My Business Nearly Broke Me25 Aug 2026
  2. Dashboard: Is Staying Small Selfish?21 Aug 2026
  3. With My New Rent, I Will Clear Nothing18 Aug 2026
  4. Dashboard: It’s Not That Earnouts Are Bad. It’s That Bad Earnouts Are Bad14 Aug 2026
  5. My Succession Plan Just Moved to Montana11 Aug 2026
  6. Dashboard: The Problem with Retainers (and Other Lessons for Solopreneurs)7 Aug 2026
  7. You’re Pre-Qualified for a 13% Loan! (That Really Costs 170%)4 Aug 2026
  8. Dashboard: The ESOP Risk Nobody Talks About31 Jul 2026
  9. ‘I Want My Employees Building My Business, Not Theirs’28 Jul 2026
  10. Dashboard: Why Open Books and Employee Ownership Aren't Enough24 Jul 2026